Executive Assistant

About The Company Trolley is a rapidly expanding creative operations company specializing in delivering high-impact digital and marketing solutions. We partner with high-profile clients to strategize, produce, and optimize compelling content that enhances engagement, boosts brand visibility, and drives business growth. Our team operates as a fully integrated powerhouse, combining strategic planning, innovative design, production excellence, and performance analysis to achieve world-class results. Built on a Founder Mode operating philosophy, Trolley emphasizes ownership, strategic thinking, and rapid execution. We foster a high-trust, collaborative environment where initiative, resourcefulness, and clear communication are valued. Our culture encourages leveraging cutting-edge tools like AI to optimize workflows, scale operations efficiently, and deliver impactful outcomes. We are committed to creating a dynamic, innovative, and growth-oriented workplace that attracts top talent globally.

About The Role We are seeking an elite-level Executive Assistant (EA) to support our CEO and Managing Partner in a full-time, remote capacity within PST or EST time zones. This role demands a proactive, decisive, and highly organized professional who thrives in high-stakes environments. The ideal candidate will be ten steps ahead, capable of managing complex relationships, optimizing workflows, and executing flawlessly across both professional and personal domains. This is not a passive support role; it requires ownership, strategic thinking, and the ability to anticipate needs before they arise. You will coordinate high-profile travel, oversee negotiations, manage critical relationships, and eliminate distractions to enable the executive to focus on big-picture strategy and execution. The position offers flexibility for occasional evening and weekend support, with a focus on high-level operational excellence and strategic influence.

Qualifications

• Proven experience supporting C-level executives, preferably CEOs or founders
• Exceptional organizational and time management skills
• Strong negotiation skills, especially in travel, luxury bookings, and vendor relationships
• Excellent communication skills, both written and verbal
• High level of discretion and confidentiality
• Proficiency with CRM systems, calendar management tools, and productivity software
• Ability to operate independently with minimal supervision
• Strong problem-solving and critical thinking abilities
• Adaptability to fast-paced, high-pressure environments
• Experience with personal and household management is a plus
• Fluency in English; additional language skills are advantageous

Responsibilities

• Coordinate and book elite travel arrangements, including international flights, accommodations, and exclusive experiences, ensuring VIP treatment and seamless itineraries
• Negotiate with vendors and service providers to secure upgrades, discounts, and special perks
• Manage the executive’s calendar, proactively resolving conflicts and prioritizing commitments aligned with strategic goals
• Oversee relationships with investors, advisors, and high-profile partners, ensuring smooth communication and follow-up
• Handle luxury shopping, including sourcing rare or high-demand items, negotiating deals, and managing refunds or returns
• Serve as a gatekeeper and trusted point of contact for key stakeholders, managing strategic outreach and correspondence
• Maintain and update CRM and investor tracking systems, ensuring accurate and timely follow-ups
• Coordinate personal logistics such as household management, family events, and wellness appointments
• Oversee vendor relationships for household and personal needs, ensuring quality and timeliness
• Manage medical records, prescriptions, and wellness-related scheduling
• Assist with strategic gifting, event planning, and special family experiences to ensure flawless execution
• Identify operational inefficiencies and implement solutions to improve workflows and productivity
• Support the executive in high-stakes negotiations, strategic initiatives, and relationship management

Benefits

• Competitive salary package commensurate with experience
• Flexible remote working environment within PST or EST time zones
• Opportunity to work closely with high-level executives and high-profile clients
• Access to cutting-edge tools and AI-driven productivity systems
• Ongoing professional development and training opportunities
• Supportive and innovative team culture focused on growth and excellence
• Work-life balance with flexibility for occasional evening and weekend support

Equal Opportunity

Trolley is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, ethnicity, gender, age, sexual orientation, disability, or any other protected characteristic. We believe that diverse perspectives and backgrounds foster innovation and drive our collective success. All qualified applicants will receive consideration for employment without regard to any protected status.